Dimethyl Sulfoxide → 1-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperazine

HRID 419610

반응식

HRID 419610 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7](F)[C:6]([Cl:10])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].Cl.[CH3:15][S:16]([CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)(=[O:18])=[O:17].C([O-])([O-])=O.[K+].[K+].CS(C)=O>O>[Cl:10][C:6]1[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[N:24]1[CH2:23][CH2:22][N:21]([CH2:20][CH2:19][S:16]([CH3:15])(=[O:17])=[O:18])[CH2:26][CH2:25]1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 534032891-Chloro-2-fluoro-4-methoxy-5-nitrobenzeneHCID 666496671-[2-(Methylsulfonyl)ethyl]piperazine hydrochloride

생성물 1

HCID 594526341-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-4-[2-(methylsulfonyl)ethyl]piperazine수율 91.3%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

To 1-chloro-2-fluoro-4-(methyloxy)-5-nitrobenzene (Example 104, Step B) (0.822 g, 4.0 mmol), 4-[2-(methylsulfonyl)ethyl]piperazine hydrochloride (Example 148, Step B) (0.915 g, 4.0 mmol), and K2CO3 (1.7 g, 12 mmol) was added DMSO (8 mL). The reaction was heated to 100° C. for two days. The reaction was determined to be complete by TLC. The reaction mixture was diluted with H2O and extracted with DCM and EtOAc sequentially for two iterations. The organic was dried (MgSO4), filtered, and rotovapped down. Purification by flash chromatography provided the title compound of Step A (1.38 g, 91%). MS (M+H, ES+) 378.

후처리

  1. extractionextracted with DCM and EtOAc sequentially for two iterations
  2. dry with materialThe organic was dried (MgSO4)
  3. filtrationfiltered
  4. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-86d4005b11134c4792f37dc014c8d999
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

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